An error has occurred with sending the test email: com.atlassian.mail.MailException: javax.mail.MessagingException: 501 Syntax: HELO hostname at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:182) at com.atlassian.jira.web.action.admin.mail.SendTestMail.doExecute(SendTestMail.java:88) at webwork.action.ActionSupport.execute(ActionSupport.java:153) at com.atlassian.jira.action.JiraActionSupport.execute(JiraActionSupport.java:57) at webwork.dispatcher.GenericDispatcher.executeAction(GenericDispatcher.java:132) at com.atlassian.jira.web.dispatcher.JiraServletDispatcher.service(JiraServletDispatcher.java:185) at javax.servlet.http.HttpServlet.service(HttpServlet.java:802) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:252) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.jira.web.filters.AccessLogFilter.doFilter(AccessLogFilter.java:51) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.opensymphony.module.sitemesh.filter.PageFilter.parsePage(PageFilter.java:119) at com.opensymphony.module.sitemesh.filter.PageFilter.doFilter(PageFilter.java:55) at com.atlassian.jira.web.filters.SitemeshExcludePathFilter.doFilter(SitemeshExcludePathFilter.java:38) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.seraph.filter.SecurityFilter.doFilter(SecurityFilter.java:182) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.seraph.filter.LoginFilter.doFilter(LoginFilter.java:181) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.util.profiling.filters.ProfilingFilter.doFilter(ProfilingFilter.java:132) at com.atlassian.jira.web.filters.ProfilingAndErrorFilter.doFilter(ProfilingAndErrorFilter.java:35) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.jira.web.filters.ActionCleanupDelayFilter.doFilter(ActionCleanupDelayFilter.java:39) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.johnson.filters.JohnsonFilter.doFilter(JohnsonFilter.java:91) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.jira.web.filters.gzip.GzipFilter.doFilter(GzipFilter.java:72) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at com.atlassian.core.filters.AbstractEncodingFilter.doFilter(AbstractEncodingFilter.java:37) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:202) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:173) at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:213) at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:178) at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:126) at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:105) at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:107) at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:148) at org.apache.coyote.http11.Http11Processor.process(Http11Processor.java:856) at org.apache.coyote.http11.Http11Protocol$Http11ConnectionHandler.processConnection(Http11Protocol.java:744) at org.apache.tomcat.util.net.PoolTcpEndpoint.processSocket(PoolTcpEndpoint.java:527) at org.apache.tomcat.util.net.LeaderFollowerWorkerThread.runIt(LeaderFollowerWorkerThread.java:80) at org.apache.tomcat.util.threads.ThreadPool$ControlRunnable.run(ThreadPool.java:684) at java.lang.Thread.run(Thread.java:595) Caused by: javax.mail.MessagingException: 501 Syntax: HELO hostname at com.sun.mail.smtp.SMTPTransport.issueCommand(SMTPTransport.java:1250) at com.sun.mail.smtp.SMTPTransport.helo(SMTPTransport.java:774) at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:316) at javax.mail.Service.connect(Service.java:233) at javax.mail.Service.connect(Service.java:134) at javax.mail.Service.connect(Service.java:86) at com.sun.mail.smtp.SMTPTransport.connect(SMTPTransport.java:144) at javax.mail.Transport.send0(Transport.java:150) at javax.mail.Transport.send(Transport.java:80) at alt.javax.mail.TransportImpl.send(TransportImpl.java:18) at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:168) ... 50 more